(E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester
CAS No.:476688-07-0
Molecular Formula:C₃₁H₄₈O₇Si
Molecular Weight:560.803
Hs Code.:

(E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester

Synonyms:(E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester

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Chemical Property of (E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester

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Technology Process of (E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester

There total 15 articles about (E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 476688-05-8
(E)-4-((4aR,5aS,8R,9S,10aR,11aS)-8-Hydroxy-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl)-2-methyl-but-2-enoic acid ethyl ester

: 476688-07-0
(E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;
DOI:10.1021/ol026804w

Reference yield:

: 50907-65-8
2-deoxy-D-erythro-pentose cyclic 1,3-propanediyl mercaptal

: 476688-07-0
(E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: CSA / CH₂Cl₂ / 20 °C

2.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

3.1: 98 percent / MeI; NaHCO₃ / H₂O; acetonitrile / 20 °C

4.1: 95 percent / SmI₂ / methanol; tetrahydrofuran / 0 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

6.1: DIBAH / CH₂Cl₂ / 0 °C

7.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

8.1: NaI / acetone / 60 °C

9.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

9.2: 100 percent / SiO₂; H₂O

10.1: TBAF / tetrahydrofuran / 20 °C

11.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

12.1: 84 percent / SmI₂ / methanol; tetrahydrofuran / 20 °C

13.1: 100 percent / DIBAH / toluene / -78 °C

14.1: 100 percent / toluene / 100 °C

15.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; samarium diiodide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium iodide; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone; toluene; acetonitrile; 2.1: hetero-Michael reaction / 11.1: hetero-Michael reaction / 14.1: Wittig reaction;
DOI:10.1021/ol026804w

Reference yield:

: 4-((4aR,6S,7R,8aS)-7-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butan-2-one

: 476688-07-0
(E)-4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-2-methyl-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: N-methylmorpholine / CH₂Cl₂ / 20 °C

2: 84 percent / SmI₂ / methanol; tetrahydrofuran / 20 °C

3: 100 percent / DIBAH / toluene / -78 °C

4: 100 percent / toluene / 100 °C

5: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; samarium diiodide; diisobutylaluminium hydride; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: hetero-Michael reaction / 4: Wittig reaction;
DOI:10.1021/ol026804w